Hello! I have been researching the structure of Cyanic acid. And I have difficulty seeing how the Isocyanate ion could be more abundant and more
stable than the Cyanate ion. Would this be also true for its acid counterparts?
For example:
With my limited knowledge of resonance structures, Isocyanic acid and cyanic acid are both isomers specifically tautomers, not resonances.
Once deprotonated then they become resonance structures.
I assumed the electronegative oxygen is where the negative charge, hydrogen proton or a metal cation are all located. Why would it be so common in
this case for the nitrogen to posses the negative charge when it is neutralized? And will protonating something like sodium cyanate result in a
majority cyanic acid or isocyanic acid?
I appreciate the help.DraconicAcid - 2-7-2020 at 12:37
As I understand it, there is no isocyanate ion- deprotonation of isocyanic acid and cyanic acid both give the same anion. I'm surprised to learn that
isocyanic acid is more stable than cyanic acid, but as you point out, they are tautomers- they will always be in equilibrium.
If you have an ionic compound, the metal cation will not be "located" on either the N or the O. There aren't any covalent bonds between the metal
cation and the cyanate anion. If you have a coordination compound, then the cyanate may be a O-bound or N-bound cyanato ligand.
In organic chemistry, isocyanates will have the organic group on the nitrogen, and cyanates will have the organic group on the oxygen.Bedlasky - 2-7-2020 at 16:09
I'm surprised to learn that isocyanic acid is more stable than cyanic acid, but as you point out, they are tautomers- they will always be in
equilibrium.
